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Direct Transformation of Arylamines to Aryl Halides via Sodium Nitrite and N ‐Halosuccinimide
Author(s) -
Mukhopadhyay Sushobhan,
Batra Sanjay
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201803347
Subject(s) - halide , chemistry , sodium nitrite , aryl , nitrite , amine gas treating , diazo , sodium azide , metal , sodium , medicinal chemistry , organic chemistry , alkyl , nitrate
Abstract A one‐pot universal approach for transforming arylamines to aryl halides via reaction with sodium nitrite (NaNO 2 ) and N ‐halosuccinimide (NXS) in DMF at room temperature under metal‐ and acid‐free condition is described. This new protocol that is complementary to the Sandmeyer reaction, is suggested to involve the in situ generation of nitryl halide induce nitrosylation of aryl amine to form the diazo intermediate which is halogenated to furnish the aryl halide.